Methanol → 6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid methyl ester

HRID 2168776Notes

Reaction equation

HRID 2168776 reaction equation
[CH2:1]([C:5]1[N:6]=[N:7][C:8](Cl)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[CH3:25][OH:26].[C]=O.CN([CH:32]=[O:33])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:25][O:26][C:32]([C:8]1[N:7]=[N:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=2)[CH:9]=1)=[O:33]

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 866577793-Butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazineHCID 178418416HCID 178418416, compound

Product 1

HCID 673717256-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178479791HCID 178479791, compoundCatalyst

Procedure

To a stirred solution of 3-butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazine (Example 14, 29 mmol, 10.0 g) in mixture of methanol and DMF (1:1, 100 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) PdCl2 (10 mol %, 2.2 g), DPPF (10 mol %, 1.6 g) and TEA (72.5 mmol, 10 mL). The reaction was stirred at 90° C. under 40-50 psi pressure of carbon monoxide for 8 h. The solvent was removed, and the crude product was purified using hexane:ethyl acetate on a 330 g ISCO silica gel column to provide 6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid methyl ester (10.0 g).

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-f26748c483c74c5cb975651bc8e93ac1
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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